aromatic compounds Flashcards
what are the three pieces of evidence to show benzene does not show the Kekule proposed structure
1 benzene is more stable than expected
2 all C-C bond lengths are the same
3 benzene doesn’t easily undergo addition reactions
what does benzene require to react with Br2
catalyst and reflux
why is benzene less reactive than expected
the 6 P electrons are delocalised over the ring which stabilises it
combustion of methyl benzene produces (flame not product)
a VERY smoky yellow flame
(high carbon to hydrogen ratio)
combustion of cyclohexene produces
a smoky yellow flame
reaction of methylbenzene with bromine water at room temperature
no reaction (requires a catalyst)
reaction of cyclohexene with bromine water at room temperature (observation)
orange solution becomes colourless
equation for methoxybenzene with a chloroalkane (with AlCl3 catalyst and heat)
C6H5OCH3 + RCA –> C6H4OCH3R + HCl
conditions for methoxybenzene and chloroalkane
heat
AlCl3 catalyst
observations of methoxybenzene and chloroalkane (4)
effervescence
damp blue litmus paper turns red
steamy fumes
white smoke with NH3
equation for nitration of methoxybenzene
C6H5OCH3 + HNO3 –> C6H4OCH3NO2 + H2O
what is an electrophile
a species which can accept a lone pair of electrons
which mechanism does benzene react with
electrophillic substitution
3 steps of an electrophilic substitution mechanism
1 formation of the electrophile
2 pair of electrons drawn from the ring to form a dative covalent bond with electrophile and reformation of the ring
3 regeneration of the catalyst
reagents and conditions for nitration of benzene (electrophilic substitution)
conc nitric acid and conc H2SO4 catalyst
heat at 55 degrees